Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 485755-36-0
• Molecular Formula: C₄₉H₅₂N₂O₁₂S
• Molecular Weight: 893.024
• Mol file: 485755-36-0.mol

Synonyms:Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester → Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (485755-36-0)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; water;

DOI:10.1039/b205031e

Reference yield:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (197702-06-0) → Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (485755-36-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: H₅IO₆ / ethyl acetate

1.2: aq. NaOH / tetrahydrofuran

1.3: 82 percent / NaBH₄

2.1: 85 percent / DMAP / pyridine

3.1: aq. AcOH / 90 °C

4.1: DMAP / pyridine

5.1: 67 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

6.1: 81 percent / NaOMe / methanol

7.1: 70 percent / pyridine

8.1: pyridine

9.1: NaH / tetrahydrofuran

10.1: aq. OsO₄; NaIO₄ / dioxane

11.1: NaBH₄ / H₂O; dioxane

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; periodic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; ethyl acetate; acetonitrile;

DOI:10.1039/b205031e

Reference yield:

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (457067-99-1) → Toluene-4-sulfonic acid (2S,3S,4R,5R)-3-benzyloxy-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(2-hydroxy-ethyl)-4-methoxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester (485755-36-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 85 percent / DMAP / pyridine

2: aq. AcOH / 90 °C

3: DMAP / pyridine

4: 67 percent / N,O-bis(trimethylsilyl)acetamide; TMS-triflate / acetonitrile / 60 °C

5: 81 percent / NaOMe / methanol

6: 70 percent / pyridine

7: pyridine

8: NaH / tetrahydrofuran

9: aq. OsO₄; NaIO₄ / dioxane

10: NaBH₄ / H₂O; dioxane

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water; acetonitrile;

DOI:10.1039/b205031e

upstream raw materials:

3-C-allyl-3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

4-C-acetoxymethyl-5-O-acetyl-3-C-allyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

4-C-acetoxymethyl-3-C-allyl-3-O-benzyl-1,2,5-tri-O-acetyl-D-erythro-pentofuranose

Downstream raw materials:

1-{(2R,3R,3aS,7aR)-3a-Benzyloxy-7a-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-methoxy-hexahydro-furo[2,3-c]pyran-2-yl}-5-methyl-1H-pyrimidine-2,4-dione